


One Night

by Winchester_Writers



Category: Supernatural
Genre: Angel Castiel, Bottom Dean, Demon Dean Winchester, M/M, Protective Sam Winchester, Top Castiel, Trickster Gabriel
Language: English
Status: In-Progress
Published: 2015-04-08
Updated: 2015-04-09
Packaged: 2018-03-21 22:55:31
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 4,027
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3706783
Author URL: https://archiveofourown.org/users/Winchester_Writers/pseuds/Winchester_Writers
Summary: <blockquote class="userstuff">
              <p>Jimmy finds Dean in a casino. This is the first time they have seen each other since high school. Dean is demon when they meet, and Jimmy believes in angels and demons. It doesn’t take time for him to figure out what he's gotten himself into.</p>
            </blockquote>





	1. Dean Winchester

**Author's Note:**

> Okay well this is written by a few people, I hope you enjoy the story, we'll be uploading a chapter each week or so. Thank you if you're reading this. Please leave comments, questions, anything.

Chapter 1- Dean Winchester 

 

Jimmy’s P.O.V.

“Hello?” I hesitantly called out to the man in the worn out leather jacket.

I don't know what came over me, or what made me stop to look at this particular man, but I was oddly pulled towards him. Something about the way he stood, the way he moved. He was hunched over some noisy gambling machine that I didn't know the name of. And, frankly, I didn't care. 

He glanced at me. “Yeah?" He had a rough voice, and as he turned his face to me, and I could've sworn I saw his eyes flash black. Shrugging it off as the dim lighting of the casino, I peered closer. His face looked eerily familiar. Then it hit me. 

“Dean? Dean Winchester? Is it you?” I think I had met him in high school, It was very surprising to me to see him there.

“Uh. Yes. What's up with you?” He looked confused for some reason.

“Dean, do you remember me?” 

“Am I supposed to...?” Ouch. 

“Jimmy. Jimmy Novak. I think we went to the same high school. Funny seeing you here.” Guess I can't blame him, it's been so long since we've seen each other, and he was only there for a week or two. Frankly, the only reason I remembered him is because he was the talk of the school. He got into fights left and right, girls swooned, guys hated him. 

"So you're, uh, Jimmy. Right." There I saw it again : his amber eyes seemed to run black again. I was only vaguely aware of the signs of demonic possession, as I was a devout Christian, but I knew when something was off. Call it a gut instinct or paranoia but, I knew something was wrong. I quickly decided to act as if everything was normal. 

“Anyways, Dean, what are you doing in Vegas?”

“Oh… Just trying out the casinos.”

“Where’s your brother?” I awkwardly tried to make conversation.

"I doubt Sam would enjoy gambling." He muttered without looking at me. 

“Yeah, I guess... so you came here alone?”

“I don't think that's any of your business, pal." He said loudly, drawing the attention of people around us. I flushed, embarrassed.

I instantly tried to hide it. I was determined to keep up with the conversation.

"Sorry if I made you upset, Dean. I was just curious," I managed to say as he stared aggressively into my eyes. I can't say that that wasn't a little erotic.

"Listen, Jimmy, is it?" He flashes something that looked like a disfigured jaw of an animal, "I’m going to put this very simply: leave me the hell alone or I will use this." 

 

Demon Dean’s P.O.V.

This guy was seriously asking for it. I continued playing on the slots to distract myself from stabbing the asshat in the chest. After a while I got annoyed 'cause the slot was taking all my coins. I moved on and saw the same 'Jimmy' guy in the corner of my eye. This guy really wanted to make my day. I looked for the nearest bathroom. It took a while to get to 'cause of the large crowds but I managed to shove people out of the way quick enough to reach my destination. Still he lurked behind me and when I entered the bathroom shortly. I grabbed him by his trench coat, "Everyone get the hell out!" I rose him up, letting his feet dangle as I waited for the bathroom to clear.

"Why are you following me?!" At this point I had my blade out and I could tell my eyes went black. I could feel the heat in my face from being so damn pissed off. 

"I'm," he choked, "I'm just curious about you." 

I've never been so confused in my life. He wasn't an angel or another demon, he was only human. I let him down but I kept a tight grip on his collar. The blade still in my closed fist.

"Who put you up to this?" I yelled, staring him, fiercely, in the eyes. A feeling struck me, like something was off about this particular man, but at the moment all I could feel was a certain sense of déjà-vu. I'd definitely seen him before, even if I couldn't remember.

The man in the trench coat met my eyes with a level sort of stare, refusing to back down - meaning he was either very stupid, very brave, or unaware of the danger he was currently putting himself in. I held the blade closer to his neck, the glinting edge of it brushing across the soft skin, but his lips only thinned. "No one did; like I said, I was just curious." His voice was flat, grating, giving away nothing. No trace of fear, but his heart pounded as if it was gonna fly out of his chest.

Curious. 

I tried to repress it, but my eyes flashed black again. That tended to happen when I was faced with things I couldn't classify - so far, he didn't seem like a threat, but I kept my guard up. There'd been more hunters trying to track me down than I cared to remember, and there was the definite possibility that he could know what I was. 

"I'm gonna ask you one last time," I inched the blade closer to his throat "what the hell do you want?" At this point I was sure I was gonna make a kill tonight, right here, right now. 

He held onto to the wrist of the hand that held the blade and lowered it from his throat. It was pretty mutual because he's not stronger than me. This really threw me off but I wasn't gonna let that show. I snarled at him but he didn't flinch. Our eyes connected once more. His heart beat slowed to a rhythmic thump as he moved our arms down to our sides. 

"Dean Winchester," he spoke finely, "I'll see you around." He let go and turned to leave the bathroom, leaving me in complete and utter shock. I didn't even think of running after him and gutting him. 

What the hell just happened? I thought over and over as I walked to the bar strip.


	2. Castiel comes (I know, crappy title)

**Summary for the Chapter:**

> Cas comes, Sam and Gabe meet and the story slowly starts to take place.

**Notes for the Chapter:**

> Please leave comments it would be awesome! Uh smut warning next chapter. Please continue reading it would be fabulous.

Jimmy’s P.O.V

As I walked out of the bathroom I could feel myself getting sick. I rushed to the nearest exit and spewed my guts out onto the streets. The fresh air calmed my raging stomach and it brought down the heat I felt all over my body. I panted heavily before catching my breath and I deciding it was time for me to sleep.

During my long walk to the hotel I thought to myself; he's not possessed, but he's a demon. That doesn't add up. I kept thinking, maybe, just maybe it's true about the mark of Cain. It has to be true. Right? I tried to shake off these thoughts as soon as I reached the hotel doors. It was a tall, gaudy building that was exactly the kind of hotel you’d expect from Las Vegas. I got into the elevator with a quick pace still confused. Wasn’t the mark of Cain applied when you had done something bad? In the bible, the mark of Cain had been applied when Cain had killed his brother. Oh no. Had Dean killed Sam? He couldn’t have. Dean loved Sam. 

I couldn't shake these questions, they ate away at me. The elevator had reached my floor and I walked the lively hallway,trying to ignore the rooms that were filled with the noises of pleasure and aggressive rummaging. I gained speed and finally arrived to my room. Closing the door behind me, I leaned my head to rest on the cool metal letting it chill my body. Still the thoughts came and went, worrying me, sickening me. I needed answers and I needed them now. I loosened my tie, tired of all this nonsense surrounding me. I had come to Vegas for vacation, a little excitement even, but demons, the Mark of Cain, was a bit too exciting for me.

I figured it was getting late, and since I had already finished my work, I could finally relax. I unbuttoned my shirt and got ready for bed. I slipped into the queen sized bed, closed my eyes, and started praying. I clasped my hands together and implored for help;

‘Oh heavens above, may you help me on this journey. I have found a friend, under the Mark of Cain, that has become a demon. May you try to help this man in distress, so that thus demons will be part of him no more. Please listen and answer to these prayers, my lord.’ I then got comfortable under the covers, and allowed myself to drift asleep.

Suddenly, a bright light flooded the room and woke me from my sleep. I shielded my eyes with my hand and squinted at the clock. 4:30 am. I looked back up at the light, and heard a voice talking to me.

“Jimmy Novak,” it thundered. It was strange, like the voice wasn’t even a voice, just a manifestation of one in my head. Am I dreaming? “I am an angel of the Lord. My name is Castiel.” 

I couldn’t stifle my surprised gasp. God had listened to me. They had come to help. 

“Who is this man that is under the Mark of Cain influence?” 

“Dean.” I answered. “Dean Winchester.” 

There was a pause. “There is only one option, Jimmy Novak. You are a suitable vessel. Your bloodline is... unique, allowing you and your family to comfortably have an angelic presence inside of you. You will have to give your body to me. I will walk around in your human body. It is the only way for me to take care of this.” 

“W-wait.” I staggered. They wanted me to give up my body? Why? Why me? 

“Jimmy, this is your mission from the Lord. You were born to be my vessel. It runs in your blood. However, I cannot take possession of your body without your permission. I don't have much time. Jimmy Novak, do you accept me?” 

Was I really considering this? This is crazy! Giving up my body? What about my family? What about my life? “And in return?” I asked shakily. 

“I can grant you a request in return for your services.” 

A request? Anything I want? “I want my family to be safe, and that demons will never harm them, as well as other creatures from under.” This time I was sure. I wanted my family safe. I wanted my parents to be safe for the rest they had of their lives. My future meant nothing if my family wasn’t there. 

“I can assure you, your family will be safe. Demons will never lay eyes on them, along with an unholy spirits. I can grant you this wish. Are you ready?” 

I was shaking so bad I couldn’t move. To tell you the truth, I was terrified. 

“Jimmy Novak, do you accept me?” The angel asked once again. 

“Yes.” I answered before I could talk myself out of it. Before I knew it, I was burning with the light and I felt myself being engulfed in a mighty flame…

 

Castiel's P.O.V. 

The vessel was small for my true form, but he was strong. I’d never get used to this feeling of being confined in a human body, despite having done it many times before. I looked down at his - no, my tie. It’s tight against my neck. I loosened it and walked out of the hotel to get some fresh air. Dean Winchester - I had raised him from hell a few years back. That was the first, and last, time we’d ever met, but he was infamous in Heaven. 

“That’s not a bad look on you, little bro.” The sarcastic voice rang out from behind me. “The tie matches your eyes. So, what’s the situation? It’s not often you decide to hitch a ride on the mundie-train.”

“It’s Dean Winchester,” I turned towards around to face Gabriel. “he possesses the Mark of Cain.” 

“I’ve heard.” The amusement drains from his face, and he gives me a stern look. “I’ve also heard that he recently slaughtered some of our own - angels, 4 of them. What makes you think he won’t smite you?” 

“I have faith in my capabilities.” 

“I’m serious, Castiel. You’re going to get hurt.” He sighs in frustration and walks up to me, reaching for my tie. “Do I have to babysit you? You can’t even wear a tie.” He ties it correctly. “I have more knowledge of humans, and frankly, I’m a lot stronger than you.” 

“No, he’ll suspect something if we both show up. I have to do this myself.” 

“Because Daddy told you so?” He snickers and steps back. “Alright, fine, it’s your funeral. I also heard that Sam Winchester is in town. That could be an issue, huh?” 

“Possibly. Does he know about Dean?” 

“He’s in danger if he goes anywhere near Dean, regardless. Should I… er… steer him off course?” 

“Yes, of course. That should buy us some time.” As soon as I said these words, Gabriel disappeared from my sight.


	3. Angel x Demon

**Notes for the Chapter:**

> Smut warning sometime in the chapter. Hehehe

Demon Dean’s P.O.V

"-and don't come back!" The bouncer barked after me. Yeah, I was wasted. That was my intention. I drank excessive amounts of alcohol, more than enough to kill a human. I stumbled, hopefully, in the direction of my hotel. The streets were crowded and full with equally wasted people so I wasn't the only one. Eventually, I found my way to the building and and the lobby was oddly quiet. So quiet I had to fill the noise with my thoughts. Jimmy... wait no... yes... ugh. At that point I was arguing with myself in my head. Stumbling, I reached the elevator and I saw him. It hit me. I saw the familiar halo that was tucked away in the recesses of my brain. The halo enveloped inside of him. What was this feeling washing over me? It was like gratitude mixed with lust mixed with fear. I couldn't make it out.

"Dean Winchester," the voice was a low grumble, a lot different from what I heard previously today. I didn't care. He wasn’t the same person I talked to earlier. I knew he's an angel, but there was something familiar about him. I couldn't form the name in in my head. Could've been from the excessive drinks or the memory swipe, but I knew this angel was no ordinary angel. 

I stepped into the elevator, trying to hold my balance. I gripped the railings so hard, my knuckles went white. 

"What's your name?" I managed to ask. He stared at me, studying me. 

"My name is Castiel," he started hesitantly, "or Cas, as you once called me before." And like a rush, memories started to flow. Like a dam being broken inside my head. It was like a puzzle, all of the missing pieces clicked together in perfect harmony. So this is what it was like for Sam. A burning wave of images flooded my mind and I hit the ground.

And it seemed to be at the worse time, but Cas helped me up and guided me to my room. Whether from the alcohol or the confusion, the world was tilting against my will, the familiar nauseous feeling biting at my stomach. I shoved Cas off and managed to make it to the bathroom just in time. 

 

Cas’s P.O.V

 

“Are you… drunk?” I asked sternly, but curiously.

“Not particularly,” he answered, sarcastically.

“This is not the time to be sarcastic. We need to talk.” I retorted.

Dean stumbles out and finishes wiping his mouth. He looks into the mini fridge and pulls a refreshing bottle of water to repress the disgusting taste of regurgitation from his mouth. He flopped down on the messy bed, taking another sip of the cool water, and looked over at me as if he’s searching for something.

“Dean…” I respond reproachfully.

“Listen, man, if you want to talk then lets talk. I’m too drunk for this anyway.” Dean leaned against the headrest of the bed and gazed at me like he was queuing me to speak.

“Dean,” I hesitated at first. “What do you remember?”

He took a deep breath and took another sip of water. He seemed be coming up with the right words either that or stalling. Either way I wasn’t expecting him to fully tell me everything on his mind. It’s Dean Winchester for my dad’s sake.

He gave me the most sinister smile I’ve ever seen on a man’s face. It made my whole body go cold. The next thing I knew he was on his feet and I was against the wall in seconds. His eyes flicked black and he chuckled maniacally.

“You wanna know what I remember Cas?” He spat. “I remember a weak little angel that always followed orders and was such a goody two shoes for us Winchesters. Do know how easy it would be to kill you right now, you spineless, feathered son of a bitch?” He studied me, my facial expressions and my eyes. I did the same.

“Dean, don’t make me hurt you.” I pleaded

Dean roared with laughter, making my body shake all over. “You? Hurt me?” His laughter continued and I could feel my face becoming hot and my concern turned to anger. 

I pushed the cackling demon off and he stumbled backwards.

“Oh, is that all you got?” He said with a sly grin “Bring it on, Wing Boy.”

I didn’t want to fight, but if this what it took then I was willing to do whatever. I wasn’t exactly ready for a fight but this needed to happen apparently. I got into a stance as if I was about to wrestle and he did the same. He punched me square in the jaw, which hurt much more than when he did it as a human. I went for a right hook, but he blocked it and hit me in my gut. I instantly doubled over and got back up all the same.

“What’s the matter Cas, am I too tough for you now?” Dean mocked.

 

I stayed silent as I realized something. If Dean wanted to kill me he would’ve done it already. What is he doing?

I began to smile as I was pinned against the wall once again. I’ve seen banter like this before, it wasn’t as rough but I know what’s happening. I’ve spent enough time to learn more from the pizza man.

“What are you smiling at? I’m kicking your ass.” Dean said, confusingly.

I reversed us, pinning him to the wall. My anger then turned to lust. I studied him like he did to me before. The confusing look stayed plastered on his face as i gripped tighter on his collar. In a flash our lips were touching. It was like a match finally getting lit and it burned so hot. Both of us fought for control but I knew I was coming out on top. My trench coat fell effortlessly to the ground. Switching positions once again, I pushed Dean down on the bed, he was rushing to get his clothes off. I’ve never seen someone so eager. 

 

Demon Dean’s P.O.V.

 

Fucking finally! I thought. I’ve been waiting so long for this. I rushed to strip as I watched my angel do the same. I was throbbing in my pants and I couldn’t wait another second for him to be inside me. When I was down to my boxers I pulled him closer by the buckle of his pants. I could see the outline of his throbbing member through his black pants. Cas looked down at me with his piercing blue eyes that made me feel like I was surrounded by a calm ocean. I unbuckled his belt slowly, teasing both him and I. I was pretty new at this whole thing so I was taking my time. I guess he couldn’t wait so he took over and unbuckled his pants for himself. I could see his cock more and it was bigger than expected which made me a bit nervous. I pressed my hand to his waist and slowly slid it down taking his boxers with it. His flaring cock twitched and I held back a gasp.

This is the first penis I’ve ever touched besides mine so I had a shaky hand.

“Relax, Dean.” Cas said so cooly it almost came out as a whisper. His hand came down to my jaw and he stroked my cheek. In that moment I felt human again. It was a good feeling.

With a steadier hand I gripped his dick and instantly my mouth started to water. I’ve never craved someone so much in my life. Teasing him, I stroked him slow and inched my mouth closer to the head of it. He was anxiously waiting and I grinned softly. Finally, I brung his tip to my tongue and I could hear the pleasuring sigh he let out. 

Cas then moved his hand to the top of my head and gripped a fist full of hair as he thrust forward sending his cock to the back of my throat. At that point I blushed for the first time since I’ve been a demon and my eyes grew to the size of quarters. I looked up at the beautiful man and stared into those captivating eyes. He looked down at me and I flicked my eyes black making him thrust faster. I could feel him growing bigger inside of my mouth. This was all so new but I couldn’t help but love it. My own cock was begging for attention so I decided to stroke myself through my boxers. 

I moaned softly, yearning for the angel’s cock to be in me. I managed to slip off my underwear and jerked myself harder.

“Dean,” Cas moaned, “I want to be in you.” this made me more horny than I’ve been since we started.   
“Cas please fuck me.” I moaned back. In an instant I was on all fours offering my virgin hole to the horny angel. I reached in the nightstand and pulled out a condom and lube. “Put this on.” I handed him the condom.

“Dean,” he started “um I don’t know how to put this on.” Laughing to myself I helped the clueless angel with the piece of rubber. After helping him I got back into my position and lubed up. To test myself I slipped a finger in giving myself an unimaginable pleasure. I repeated this a couple times until I knew I was fully ready.

“Cas.” I said pleadingly. I felt him teasing my hole with his tip. Then I felt the pleasuring pain of myself stretching as he entered me. I tried to repress the instinct to grunt but i couldn’t hold it in.

“What’s the matter Dean.” Cas chuckled “am I too tough for you now?” I chuckled along with him until he thrusted again and the chuckle instantly turned into a loud moan. I moaned louder as Cas’ pumps became deeper and harder. I’ve never had something satisfactory. Not even my favorite pie could match this. I grunted and moaned louder as he increased his speed. As he fucked me I stroked myself I was so close to my climax.

“Oh fuck!!” I exclaimed “I’m gonna cum, Cas!” I stroked myself faster matching the speed of Cas. 

“Not yet, Dean.” He said back, but I felt like I was going to explode. He sped one final time and like that we climaxed together. “Fuck!” Cas sighed and instantly turned red from embarrassment.

“Oh, don’t be so modest now. You just broke Heaven’s number one rule.” I lied, panting, covered in sweat and other fluids. He lied next to me panting as well. I was pleased and tired and by the looks of it so was he.


End file.
